If you're struggling on (1), Reddit has all kind of bizarre subreddits which cater to all kinds of images. It's also conveniently (is that fortunate?) well categorised. There are definitely subs for gory photos, non-nudity NSFW images and so on. Reddit is also a great resource for categorised SFW, since there are so many subreddits with active and strict moderation.

It's reasonably easy to scrape: https://github.com/jveitchmichaelis/redditdownloader

They may have changed the API since I wrote that though.